Synthesis of N(ε)-(p-bromophenyl)-L-lysine and N(τ)-(p-bromophenyl)-L-histidine as models for adducts of bromobenze 3,4-oxide to protein. Observation of an unusual Pd-catalyzed N(τ)- to N(π)-aryl substituent migration

Article abstract of DOI:10.1021/jo00083a011

Bromobenzene 3,4-oxide (1), the putative toxic metabolite of bromobenzene, is known to alkylate protein sulfur nucleophiles in vivo and is postulated to alkylate protein nitrogen nucleophiles, the expected products of which would include, after hydrolysis